Process for preparing fatty acid esters

Abstract

A process for reacting (1) a component selected from the group consisting of sterols and branched aliphatic primary or secondary alcohols having 14 to 32 carbon atoms, and (2) a component selected from the group consisting of fatty acids and fatty acid esters in contact with an enzyme selected from the group consisting of lipase and cholesterol esterase or with the selected enzyme in an immobilized form, in a system selected from the group consisting of an aqueous medium and water-containing organic solvent to prepare a fatty acid ester of the component (1).

We claim: 
     
       1. A process for preparing a fatty acid ester, the process consisting essentially of reacting: (1) a component selected from the group consisting of cholesterol, β-sitosterol, stigmasterol, β-cholesterol, ergosterol, isocholesterol, campesterol, brassicasterol and isotridecyl alcohol and   (2) a component selected from the group consisting of fatty acids and fatty acid esters,   in contact with a lipase derived from a microorganism selected from the group consisting of Candida cylindracea, Pseudomonas fluorescens, Pseudomonas fragi, Chromobacterium viscosum, Aspergillus niger, and Rhizopus delemar, in a reaction system consisting essentially of the component (1), the component (2), the lipase, and either water or a water-containing organic solvent,   and recovering the product fatty acid ester from the resulting mixture.   
     
     
       2. A process as defined in claim 1 wherein the component (2) is a fatty acid selected from the group consisting of saturated straight-chain fatty acids, saturated branched fatty acids, unsaturated fatty acids, hydroxy fatty acids and polycaroxylic acids having up to 32 carbon atoms. 
     
     
       3. A process as defined in claim 1 wherein the component (2) is a member selected from the group consisting of natural oil, natural fat, synthetic oil, synthetic fat, natural wax and synthetic wax. 
     
     
       4. A process as defined in 1 wherein the component (2) is a glycerin ester of a fatty acid having up to 32 carbon atoms. 
     
     
       5. A process as defined in 1 wherein the component (2) is an ester of aliphatic alcohol having 1 to 14 carbon atoms. 
     
     
       6. A process as defined in 1 wherein the reaction is conducted in a water-containing organic solvent. 
     
     
       7. A process as defined in 1 wherein the water-containing organic solvent is capable of dissolving at least one of component (1) and component (2) and is an organic solvent containing water to at least saturation. 
     
     
       8. A process as defined in claim 7 wherein the water-containing organic solvent is a hydrocarbon solvent saturated with water. 
     
     
       9. A process as defined in claim 7 wherein the water-containing organic solvent comprises the two phases of water and an organic solvent. 
     
     
       10. A process as defined in claim 1 wherein the lipase is separated by phase separation, filtration or centrifugation from the resulting product mixture. 
     
     
       11. A process as defined in claim 1 wherein a porous membrane is used and the component (1) and the component (2) are brought into contact with the lipase through the micropores of the membrane. 
     
     
       12. A process as defined in claim 1 wherein the lipase is used in an immobilized state. 
     
     
       13. A process as defined in claim 12 wherein the immobilized lipase is obtained by an entrapping method using a photo-crosslinkable resin prepolymer or an urethane prepolymer as a carrier. 
     
     
       14. A process as defined in claim 12 wherein the immobilized lipase is obtained by a covalent bond method using an inorganic or organic carrier. 
     
     
       15. A process as defined in claim 12 wherein the immobilized lipase is obtained by an adsorption method using an inorganic or organic carrier. 
     
     
       16. A process for preparing a fatty acid ester, which comprises reacting a component (1) and a component (2) in contact with a cholesterol esterase in a reaction system consisting essentially of said component (1), said component (2), said cholesterol esterase and a water-containing organic solvent, wherein component (1) being at least one member selected from the group consisting of cholesterol, isocholesterol, campesterol, stigmasterol, β-sitosterol, brassicasterol, β-cholestanol, 2-octyldodecanol, Lanolin alcohol HH and a branched aliphatic saturated alcohol represented by the following formula: ##STR8## component (2) being at least one member selected from the group consisting of fatty acids and fatty acid esters in contact with a cholesterol esterase derived from Candida cylindracea, and   recovering the product fatty acid ester from the resulting mixture.   
     
     
       17. A process as defined in claim 16, wherein the water-containing organic solvent is capable of dissolving at least one of component (1) and component (2) and is an organic solvent containing water to saturation. 
     
     
       18. A process as defined in claim 17, wherein the water-containing organic solvent is a hydrocarbon solvent saturated with water. 
     
     
       19. A process as defined in claim 17, wherein the water-containing organic solvent comprises the two phases of water and an organic solvent. 
     
     
       20. A process as defined in claim 11, wherein the component (2) is a fatty acid selected from the group consisting of saturated straight-chain fatty acids, saturated branched fatty acids, unsaturated fatty acids, hydroxy fatty acids and polycarboxylic acids having up to 32 carbon atoms. 
     
     
       21. A process as defined in claim 16, wherein component (2) is a member selected from the group consisting of natural oil, natural fat, synthetic oil, synthetic fat, natural wax and synthetic wax. 
     
     
       22. A process as defined in claim 16, wherein the component (2) is a glycerin ester of fatty acid having up to 32 carbon atoms. 
     
     
       23. A process as defined in claim 16, wherein the component (2) is an ester of aliphatic alcohol having 1 to 14 carbon atoms. 
     
     
       24. A process as defined in claim 16, wherein the cholesterol esterase is separated by phase separation, filtration or centrifugation from the resulting product mixture. 
     
     
       25. A process as defined in claim 16, wherein a porous membrane is used and the component (1) and the component (2) are brought into contact with the cholesterol esterase through the micropores of the membrane. 
     
     
       26. A process as defined in claim 16, wherein the cholesterol esterase is used in an immobilized state. 
     
     
       27. A process as defined in claim 26, wherein the immobilized cholesterol esterase is obtained by an entrapping method using a photo-crosslinkable resin prepolymer or an urethane prepolymer as a carrier. 
     
     
       28. A process as defined in claim 26, wherein the immobilized cholesterol esterase is obtained by a covalent bond method using an inorganic or organic carrier. 
     
     
       29. A process as defined in claim 26, wherein the immobilized cholesterol esterase is obtained by an absorption method using an inorganic or organic carrier. 
     
     
       30. A process for preparing a fatty acid ester, which comprises reacting a component (1) and a component (2) in contact with a cholesterol esterase in a reaction system consisting essentially of said component (1), said component (2), said cholesterol esterase and a water-containing organic solvent, wherein component (1) being at least one member selected from the group consisting of cholesterol, β-sitosterol, isocholesterol, campesterol, stigmasterol, β-sitosterol, brassicasterol, β-cholestanol, 2-octyldodecanol, Lanolin alcohol HH and a branched aliphatic saturated alcohol represented by the following formula: ##STR9## component (2) being at least one member selected from the group consisting of fatty acids and fatty acid esters in contact with cholesterol esterase T-18, and   recovering the product fatty acid ester from the resulting mixture.   
     
     
       31. A process as defined in claim 30, wherein the water-containing organic solvent is capable of dissolving at least one of component (1) and component (2) and is an organic solvent containing water to saturation. 
     
     
       32. A process as defined in claim 31, wherein the water-containing organic solvent is a hydrocarbon solvent saturated with water. 
     
     
       33. A process as defined in claim 31, wherein the water-containing organic solvent comprises the two phases of water and an organic solvent. 
     
     
       34. A process as defined in claim 30, wherein the component (2) is a fatty acid selected from the group consisting of saturated straight-chain fatty acids, saturated branched fatty acids, unsaturated fatty acids, hydroxy fatty acids and polycarboxylic acids having up to 32 carbon atoms. 
     
     
       35. A process as defined in claim 30, wherein component (2) is a member selected from the group consisting of natural oil, natural fat, synthetic oil, synthetic fat, natural wax and synthetic wax. 
     
     
       36. A process as defined in claim 30, wherein the component (2) is a glycerin ester of fatty acid having up to 32 carbon atoms. 
     
     
       37. A process as defined in claim 30, wherein the component (2) is an ester of aliphatic alcohol having 1 to 14 carbon atoms. 
     
     
       38. A process as defined in claim 30, wherein the cholesterol esterase is separated by phase separation, filtration or centrifugation from the resulting product mixture. 
     
     
       39. A process as defined in claim 30, wherein a porous membrane is used and the component (1) and the component (2) are brought into contact with the cholesterol esterase through the micropores of the membrane. 
     
     
       40. A process as defined in claim 30, wherein the cholesterol esterase is used in an immobilized state. 
     
     
       41. A process as defined in claim 40, wherein the immobilized cholesterol esterase is obtained by an entrapping method using a photo-crosslinkable resin prepolymer or an urethane prepolymer as a carrier. 
     
     
       42. A process as defined in claim 40, wherein the immobilized cholesterol esterase is obtained by a covalent bond method using an inorganic or organic carrier. 
     
     
       43. A process as defined in claim 40, wherein the immobilized cholesterol esterase is obtained by an absorption method using an inorganic or organic carrier. 
     
     
       44. A process for preparing a fatty acid ester, which comprises reacting a component (1) and a component (2) in contact with a cholesterol esterase in a reaction system consisting essentially of component (1), said component (2), said cholesterol esterase and a water-containing organic solvent, wherein 2-octyldodecanol as a component (1) is reacted with a component (2) selected from the group consisting of capric acid and oleic acid in contact with a panaceas-derived cholesterol esterase,   and recovering the product fatty acid ester from the resulting mixture.   
     
     
       45. A process as defined in claim 44, wherein the water-containing organic solvent is capable of dissolving at least one of component (1) and component (2) and is an organic solvent containing water to saturation. 
     
     
       46. A process as defined in claim 45, wherein the water-containing organic solvent is a hydrocarbon solvent saturated with water. 
     
     
       47. A process as defined in claim 45, wherein the water-containing organic solvent comprises the two phases of water and an organic solvent. 
     
     
       48. A process as defined in claim 46, wherein the component (2) is a fatty acid selected from the group consisting of saturated straight-chain fatty acids, saturated branched fatty acids, unsaturated fatty acids, hydroxy fatty acids and polycarboxylic acids having up to 32 carbon atoms. 
     
     
       49. A process as defined in claim 46, wherein component (2) is a member selected from the group consisting of natural oil, natural fat, synthetic oil, synthetic fat, natural wax and synthetic wax. 
     
     
       50. A process as defined in claim 46, wherein the component (2) is a glycerin ester of a fatty acid having up to 32 carbon atoms. 
     
     
       51. A process as defined in claim 46, wherein the component (2) is an ester of aliphatic alcohol having 1 to 14 carbon atoms. 
     
     
       52. A process as defined in claim 46, wherein the cholesterol esterase is separated by phase separation, filtration or centrifugation from the resulting product mixture. 
     
     
       53. A process as defined in claim 46, wherein a porous membrane is used and the component (1) and the component (2) are brought into contact with the cholesterol esterase through the micropores of the membrane. 
     
     
       54. A process as defined in claim 46, where the cholesterol esterase is used in an immobilized state. 
     
     
       55. A process as defined in claim 54, wherein the immobilized cholesterol esterase is obtained by an entrapping method using a photo-crosslinkable resin prepolymer or an urethane prepolymer as a carrier. 
     
     
       56. A process as defined in claim 54, wherein the immobilized cholesterol esterase is obtained by a covalent bond method using an inorganic or organic carrier. 
     
     
       57. A process as defined in claim 54, wherein the immobilized cholesterol esterase is obtained by an absorption method using an inorganic or organic carrier.